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Ever since the days when comedy couples stopped sleeping in separate beds (where did all those sitcom kids come from anyway?), much of television comedy has been driven by a single question:  

Will they or won’t they?

20th Century Fox Television

Hell yeah, they did.

Sam and Diane on Cheers.  For that matter, Sam and Rebecca on Cheers. Ross and Rachel on Friends  Carrie and Mr. Big on Sex and the City.  Nick and Jess on New Girl. Robin and Barney on How I Met Your Mother. Leslie and Ben on Parks and Rec.  You get the picture.

Why is the trope so popular in television comedy?  That’s an easy one:  Dramatic tension + the possibility of sex = you have our complete and undivided attention.  

But just because Will They or Won’t They? is a no-brainer doesn’t make it easy for comedy writers.  If you get the couple together too quickly -- premature exultation, as it were -- you’ve lost your potential for multiple seasons’ worth of saucy storylines.

Picturemaker Productions

Desk sex tip:  Watch out for the three-hole punch!

And when the question essentially becomes the show? Then you have what critics call the Moonlighting Curse -- once Bruce Willis and Cybill Shepherd slept together, the show was essentially over. What else was there once the deed had been done?

So avoid the curse by keeping the potential lovebirds apart. Simple, right?  Well, um, no. If you carry on too long with convoluted obstacles and missed opportunities, viewers are likely to get frustrated and move on to something more interesting.  

20th Century Fox Television

For once, could the girl wear the trenchcoat and the guy wear the lacy bra?

Then there’s the They Did It But Should They Keep Doing It? question. One gets the sense that after New Girl writers allowed Jess and Nick to (prematurely?) hook up in Season 2, they panicked that the new relationship would subject their show to the Moonlighting Curse.  The solution?  Break ‘em up.  Did it work?  You decide.

Will They or Won’t They? is essential but making it work is a delicate dance. Want a good example? Let’s travel to Scranton and check in with Jim and Pam at The Office -- a well-played exercise in romantic tension that wasn’t afraid to finally pay off our patience with an actual relationship.

Jim and Pam: A Match Made In Sitcom Nirvana

Deedle-Dee Productions

A love based on a common interest in terrorizing co-workers.

When we first meet Jim and Pam, their mutual attraction is pretty obvious to anyone not named Michael Scott. All of that sexual heat can’t be solely attributed to the kink of encasing Dwight’s stapler in Jell-O. 

But how do we play out Jim and Pam’s (or any) budding romance over the course of several seasons?  The key, according to Billy Menrit, author of Writing the Romantic Comedy, is two fold:

1.  Creating obstacles to keep the couple apart, while at the same time …

2.  Convincing the audience that these two people truly do belong together.

We should mention that the obstacles should be realistic and not “Oh man, they were going to kiss until the late Betty White showed up out of the blue!”  We need real-life reasons why romance just isn’t possible right now -- but don’t rule out love’s potential entirely. Since we’re talking comedy, it helps if the obstacles are funny as well. 

So let’s go season by season, seeing how the Office writers took on both tasks.  Note the delicate balancing act -- every time the Love See-Saw goes up to show us they belong together, an Obstacle sends the Love See-Saw right back down .

Season One

Deedle-Dee Productions

The face of a man trying desperately not to move.

Only six episodes in the first season of The Office, but we’re off to a good start.  Right away, we learn that:

Pam and Jim are best friends at work.  (They belong together)

But Pam is engaged to Roy.  (Obstacle)

Pam falls asleep on Jim’s shoulder during the Diversity Day seminar. (Belong together)

But she hurries away when she wakes, feeling guilty. (Obstacle)

Jim starts dating someone -- Katy, the Hot Girl who sells purses in the office. (Obstacle)

Despite her protests that she and Jim are just friends, Pam is jealous.  (Belong together)

Season Two 

Deedle-Dee Productions

God isn't the only thing I'm feeling in this Chilis tonight.

Pam is afraid of receiving another Dundie for Longest Engagement. (Proof that Pam and Roy don’t belong together)  When she receives an award for Whitest Tennis Shoes, she kisses Jim. (Belong together)

But Pam is drunk, so the kiss isn’t ”real.” (Obstacle)

On the Booze Cruise, Pam and Jim lament their choice in dates. (Belong together)

But on the same cruise, Pam and Roy finally set a date for the wedding. (Obstacle)

A dejected Jim confesses his love for Pam to Michael.  (Belong together)

Come on, it’s Michael.  He’s going to tell every. Damn. Body. (Obstacle)

Roy finds out about Jim’s crush and confronts him. It’s resolved peacefully - for now. (Obstacle)

In the same episode, Pam won’t pursue art in part because knucklehead Roy doesn’t think it will lead to anything real.  Jim believes in Pam’s talent and tells her to take a chance. (Belong together)

Jim assures everyone that his crush on Pam is a thing of the past. (Obstacle) 

But Pam figures out that’s not exactly the truth. (Belong together)

On Casino Night, Jim finally tells Pam how he feels. (Belong together)

Pam shuts him down, begging Jim not to ruin their friendship. (Obstacle)

He kisses her anyway. On the dang mouth!  (Belong together)

A cool side note:  Notice how Season Two begins and ends with a kiss -- the first initiated by Pam and the second sealed by Jim.

Season Three

Deedle-Dee Productions

This is what a good Obstacle looks like.

Pam confesses that she’s waited a long time for that damn kiss. (Belong together)

But she’s going to honor her commitment to that warehouse idiot, Roy. (Obstacle)

Heartbroken, Jim and his tuna sandwiches transfer to Stamford. (Obstacle)

Pam misses her best friend, leading her to call off the wedding. (Belong together)

The Stamford branch is downsized and Pam is thrilled that Jim is returning to Scranton. (Belong together)

But he’s back with a smart, funny new girlfriend, Karen. (Obstacle)

Pam cries when she realizes she pushed Jim into the arms of another woman. (Belong together)

With Jim no longer available, Pam reunites with Newly Buff Roy. (Obstacle)

Pam confesses the Casino Night kiss, leading Newly Buff Roy to confront Jim. The only thing saving Jim’s ass from a severe beating is Dwight Schrute and his pepper spray.  Good thing it wasn’t encased in Jell-O.  (Obstacle)

Now done with Roy forever, Pam confesses her feelings for Jim at the beach retreat. (Belong together)

But Jim is still in a relationship with Karen and may move to New York for a job at Corporate. (Obstacle)

Jim finds good luck gifts from Pam during his job interview.  He withdraws his name from consideration for the job, breaks up with Karen, and returns to Scranton to ask Pam for a date. (Belong together)

Pam accepts!  The answer to Will They or Won’t They? is finally resolved after three seasons of build-up.  Of course they will.  

That doesn’t mean the Office writers were done with Jim and Pam. They would still throw obstacles their way -- Jim can’t find the right time to propose!  They can’t get the quiet, private wedding of their dreams!  Pam gets a job at the rival Michael Scott Paper Company!  But through it all, the relationship stays on mostly solid ground.  

That’s mature writing, but it doesn’t necessarily lead to comic fireworks.  That’s why The Office introduced a number of fresh Will They or Won’t They? scenarios over the course of its nine seasons.  Some of them were fan favorites -- Michael and Holly.  Dwight and Angela.  Ryan and Kelly.

And then there were duds:  Gabe and Erin.  Michael and Pam’s mom. (Ew.) Andy and anyone.  Hey, they can’t all be winners.  But you can’t blame the writers for throwing new relationships at the wall to see which ones stuck.  Will They or Won’t They? is the lifeblood of television comedy, especially when you’re trying to extend plotlines over multiple seasons.

How To Get It Wrong: Ross and Rachel

Warner Bros. Television

They're going to break up again after the commercial.

The Office played the game perfectly.  It avoided the Moonlighting Curse by keeping its main couple apart with realistic obstacles -- but for not so long that we were throwing Diet Coke cans at the screen in frustration.

Which brings us to Ross and Rachel. 

A Ringer analysis of “relationship uncertainty” -- those episodes when the question of Will They Or Won’t They? was in play -- found that Ross and Rachel lived in a wishy-washy state of romantic maybe for an incredible 210 shows of Friends’ 236-episode run. That’s nearly 90% of the show’s entire existence!  No wonder we didn’t care by the time Ross and Rachel finally came to their senses and realized they belonged together.

That’s after at least three break-ups, one divorce, several questions about whether Ross was cheating or they were on a break (Ross was cheating), and weird near-romances with other characters.  Seriously, Rachel and Joey?

The Ross and Rachel coupling fails on both of Menrit’s criteria for successful romantic comedy -- a belief that the characters really belong together and realistic obstacles keeping them apart.  

If they can’t get together after a decade of false starts?  Take a hint, Rachel -- maybe Ross isn’t your guy after all.  We don’t believe these two really belong together or they would have made it happen a long time ago.

As for the obstacles?  To keep these shenanigans going for ten years, Friends writers had to come up with increasingly out-there ways to keep them apart.  For Pete’s sake, their first kiss was almost thwarted because they couldn’t unlock the door at Central Perk! Then there was the pros and cons list that accidentally gets discovered.  Jealousy over coworker friendships. A drunken marriage that they barely remember. Marriages to other people. Something-something with Marcel the monkey.  Optometrists must have made a mint from all of the viewer eye-rolling.

Ross!  You’re the father of Rachel’s child!  Just be in a relationship already so we can get to the Joey spin-off. 

Here’s one trend that bodes well for the future of Will They or Won’t They -- the advent of streaming.  Actually, there are a couple of trends.  First, streaming comedies are producing far fewer episodes per season than the sitcoms that used to run on network TV.  The latest season of Ted Lasso had 12 episodes, Rick and Morty’s fourth season had ten, the same as the latest season of Cobra Kai

Compare that to 24 episodes a year for Friends.  Imagine how many fewer hoops Ross and Rachel would have had to squirm through if their romance was featured in less than half the shows?  More compact seasons mean more compact storytelling with fewer made-up barriers to keep couples apart.

The other streaming trend is finite series.  Take some of the funnier Marvel series like WandaVision and Loki. Not only do the series have a limited number of episodes, but the stories themselves are self-contained.  When a series isn’t designed to be open-ended so it can run for as many seasons as possible (streaming also means reaching syndication isn’t the goal it once was), writers can focus on the best stories, not on “how the hell do we keep these balls in the air?”

So now we leave it to the comedy writers. Will They or Won’t They be able to avoid the Moonlighting Curse?  We wish them luck -- and kindly ask them to leave  monkeys as far away from the couples as possible. 

For more ComedyNerd, be sure to check out:

Will Forte: He's Criminally Underrated

Jerry Seinfeld vs. George Carlin: The Case for Cursing in Comedy

Why The 9/11 Issue Maybe Wasn't Great For 'The Onion'?

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